(3S,10R,13S,17S)-3-((tert-butyldiphenylsilyl)oxy)-N-methoxy-N,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide | 1369391-46-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3S,10R,13S,17S)-3-((tert-butyldiphenylsilyl)oxy)-N-methoxy-N,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
• 英文别名: N-methoxy-N-methyl-3β-(t-butyldiphenylsilyloxy)-androst-5-en-17β-carboxamide
• CAS: 1369391-46-7
• 化学式: C₃₈H₅₃NO₃Si
• 分子量: 599.929
• InChiKey: AAGQMABXXLLKAA-HHVZCBCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.53
• 重原子数：
  43.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,10R,13S,17S)-3-((tert-butyldiphenylsilyl)oxy)-N-methoxy-N,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide 在 吡啶 、 1,3-二溴-5,5-二甲基海因 、 偶氮二异丁腈 、 四丁基氟化铵 、 magnesium 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 2.33h， 生成 [(3S,8S,9S,10R,13S,14S,17S)-7-bromo-10,13-dimethyl-17-(5-methylhexanoyl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
  参考文献：
  名称：

  Design, Synthesis, and Biological Action of 20R-Hydroxyvitamin D3

  摘要：

  The non-naturally occurring 20R epimer of 20-hydroxyvitamin D3 is synthesized based on chemical design and hypothesis. The 20R isomer is separated by semipreparative HPLC, and its structure is characterized. A comparison of 20R isomer to its 20S counterpart in biological evaluation demonstrates that they have different behaviors in antiproliferative and metabolic studies.

  DOI：

  10.1021/jm201478e
• 作为产物：
  描述：

  孕烯醇酮醋酸酯 在 N-甲基咪唑 、 溴 、 碘 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 (3S,10R,13S,17S)-3-((tert-butyldiphenylsilyl)oxy)-N-methoxy-N,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Action of 20R-Hydroxyvitamin D3

  摘要：

  The non-naturally occurring 20R epimer of 20-hydroxyvitamin D3 is synthesized based on chemical design and hypothesis. The 20R isomer is separated by semipreparative HPLC, and its structure is characterized. A comparison of 20R isomer to its 20S counterpart in biological evaluation demonstrates that they have different behaviors in antiproliferative and metabolic studies.

  DOI：

  10.1021/jm201478e

文献信息

• Design and synthesis of 21-alkynylaryl pregnenolone derivatives and evaluation of their anticancer activity
  作者：György Szalóki、Athanasia Pantzou、Kyriakos C. Prousis、Olga Mavrofrydi、Panagiota Papazafiri、Theodora Calogeropoulou

  DOI：10.1016/j.bmc.2014.10.012

  日期：2014.12

  A series of novel C21-alkynylaryl derivatives of pregnenolone were synthesized and screened for anticancer activity against a panel of seven human cancer cell lines (LNCaP, A549, MCF7, HeLa, A431, HepG2, HT29). The data revealed that these compounds can be potential antitumour agents against the specific cell models. Compound 6f bearing a 2-trifluoromethylphenyl group displayed improved cytotoxicity towards all cancer cell lines used. A431 cells were the most sensitive with derivatives 6e-6h bearing electron withdrawing substituents exhibiting high potency with IC50 values ranging between 2.18 and 0.54 mu M and drastic inhibition of the prosurvival PI3K-Akt/PKB pathway. (C) 2014 Elsevier Ltd. All rights reserved.